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药品详细

Cefotaxime(头孢噻肟)

化学结构式图
中文名
头孢噻肟
英文名
Cefotaxime
分子式
C16H17N5O7S2
化学名
(6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
分子量
Average: 455.465
Monoisotopic: 455.056939303
CAS号
63527-52-6
ATC分类
J01D Other Beta- lactam Antibacterials
药物类型
small molecule
阶段
approved
商品名
Claforan;
同义名
Cefotaxime sodium;Cephotaxime;
基本介绍

Cefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Sanofi-Aventis).

生产厂家
  • App pharmaceuticals llc
  • Aurobindo pharma ltd
  • B braun medical inc
  • Cephazone pharma llc
  • Hikma farmaceutica lda
  • Lupin ltd
  • Orchid healthcare
  • Sanofi aventis us llc
  • Wockhardt ltd
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
antibacterials 抗细菌;
药理
Indication Used to treat gonorrhoea, meningitis, and severe infections including infections of the kidney (pyelonephritis) and urinary system. Also used before an operation to prevent infection after surgery.
Pharmacodynamics Cefotaxime is a third generation intravenous cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotaxime works by inhibiting bacterial cell wall biosynthesis. A positive feature of cefotaxime is that it display a resistance to penicillinases and is useful to treat infections that are resistant to penicillin derivatives.
Mechanism of action The bactericidal activity of cefotaxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefotaxime shows high affinity for penicillin-binding proteins in the cell wall including PBP Ib and PBP III.
Absorption Rapidly absorbed following intramuscular injection.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite. The desacetyl metabolite has been shown to contribute to the bactericidal activity. Two other urinary metabolites (M2 and M3) account for about 20-25%. They lack bactericidal activity.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Cefotaxime
    		Desacetyl-cefotaxime Details
    Route of elimination Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite.
    Half life Approximately 1 hour.
    Clearance Not Available
    Toxicity Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions. Oral rat LD50 is over 20,000 mg/kg while intravenous rat LD50 is over 7,000 mg/kg.
    Affected organisms
    • Enteric bacteria and other eubacteria
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    water solubility Soluble Not Available
    logP -0.5 Not Available
    Predicted Properties
    Property Value Source
    water solubility 1.46e-01 g/l ALOGPS
    logP 0.14 ALOGPS
    logP -1.4 ChemAxon
    logS -3.5 ALOGPS
    pKa (strongest acidic) 3.18 ChemAxon
    pKa (strongest basic) 4.15 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 9 ChemAxon
    hydrogen donor count 3 ChemAxon
    polar surface area 173.51 ChemAxon
    rotatable bond count 8 ChemAxon
    refractivity 105.11 ChemAxon
    polarizability 41.78 ChemAxon
    药物相互作用
    Drug Interaction
    Amikacin Increased risk of nephrotoxicity
    Gentamicin Increased risk of nephrotoxicity
    Kanamycin Increased risk of nephrotoxicity
    Neomycin Increased risk of nephrotoxicity
    Netilmicin Increased risk of nephrotoxicity
    Probenecid Probenecid may increase the serum level of cefotaxime.
    Streptomycin Increased risk of nephrotoxicity
    Tobramycin Increased risk of nephrotoxicity
    食物相互作用
    Not Available

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